Sure, we all know about Manhattan's museums and old-money mansions, but an hour or so upstate lie riches on a larger scale. This is Rockefeller country we're talking about—huge estates and acres (not rooms) full of sculptures by big-name artists and views of the Hudson River. But with all this grandeur, you also have authentic rustic gems—five-and-dimes out of the '50s and family-owned restaurants that serve food grown in the local soil. Because of these diverse offerings, each leg of our journey from Tarrytown, New York, to North Adams, Massachusetts, mixes vibes—artsy, quaint, retro chic, high culture. Just pick the pit stops with the personalities that most appeal to your crew.

Day 1

Tarrytown to Dover Plains

Start in historic Tarrytown, 30 miles north of New York City, and tour Washington Irving's mid-19th-century Sunnyside Manor (West Sunnyside Ln., off Rte. 9, 914-631-8200). Next, head east to Stone Barns Center (630 Bedford Rd., Pocantico Hills, 914-366-6200). Visit the pigs, cows, and chickens on this hikeable 80-acre Rockefeller estate and working farm, then try the egg salad at the café. Continue northeast for 35 miles to Storm King Art Center (Old Pleasant Hill Rd., Mountainville, 845-534-3115) to see 100 outdoor sculptures by artists including Calder and Noguchi. Enjoy a grass-fed burger two miles north at Woody's (30 Quaker Ave., Cornwall, 845-534-1111), then head 11 miles west to see massive instal­lation art by Andy Warhol, Richard Serra, and others at Dia:Beacon (3 Beekman St., Beacon, 845-440-0100).

Stay at Old Drovers Inn, 35 miles west in Dover Plains (from $175 per night, Duncan Hill Rd. and Old Rte. 22, 845-832-9311), for ye olde charm.

Next Page: Dover Plains to Saugerties